ES2297864T3 - Pirrolopirimidinas sustituidas y procesos para su preparacion. - Google Patents

Info

Publication number

ES2297864T3

ES2297864T3 ES97940108T ES97940108T ES2297864T3 ES 2297864 T3 ES2297864 T3 ES 2297864T3 ES 97940108 T ES97940108 T ES 97940108T ES 97940108 T ES97940108 T ES 97940108T ES 2297864 T3 ES2297864 T3 ES 2297864T3

Authority

ES

Spain

Prior art keywords

formula

pyrrolo

pyrimidine

chloroanilino

radical

Prior art date

1996-08-23

Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)

Expired - Lifetime

Links

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• Global Dossier
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• 238000000034 method Methods 0.000 title claims description 50
• 238000002360 preparation method Methods 0.000 title claims description 42
• 230000008569 process Effects 0.000 title claims description 38
• -1 3 -phenylureido Chemical group 0.000 claims abstract description 212
• 125000000217 alkyl group Chemical group 0.000 claims abstract description 67
• 150000003839 salts Chemical class 0.000 claims abstract description 46
• 239000000460 chlorine Substances 0.000 claims abstract description 29
• 239000001257 hydrogen Substances 0.000 claims abstract description 24
• 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 24
• 229910052801 chlorine Inorganic materials 0.000 claims abstract description 15
• 125000003545 alkoxy group Chemical group 0.000 claims abstract description 14
• 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims abstract description 12
• 125000003282 alkyl amino group Chemical group 0.000 claims abstract description 11
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 11
• 125000004299 tetrazol-5-yl group Chemical group [H]N1N=NC(*)=N1 0.000 claims abstract description 10
• 125000001309 chloro group Chemical group Cl* 0.000 claims abstract description 9
• JJTNLWSCFYERCK-UHFFFAOYSA-N 7h-pyrrolo[2,3-d]pyrimidine Chemical class N1=CN=C2NC=CC2=C1 JJTNLWSCFYERCK-UHFFFAOYSA-N 0.000 claims abstract description 6
• 125000000437 thiazol-2-yl group Chemical group [H]C1=C([H])N=C(*)S1 0.000 claims abstract description 6
• 125000004656 alkyl sulfonylamino group Chemical group 0.000 claims abstract description 5
• 125000000972 4,5-dimethylthiazol-2-yl group Chemical group [H]C([H])([H])C1=C(N=C(*)S1)C([H])([H])[H] 0.000 claims abstract description 4
• 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims abstract description 4
• 125000005281 alkyl ureido group Chemical group 0.000 claims abstract description 3
• 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims abstract description 3
• 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims abstract 2
• 125000004356 hydroxy functional group Chemical group O* 0.000 claims abstract 2
• 150000001875 compounds Chemical class 0.000 claims description 204
• 125000001424 substituent group Chemical group 0.000 claims description 54
• 125000006239 protecting group Chemical group 0.000 claims description 51
• 239000002253 acid Substances 0.000 claims description 49
• 125000000524 functional group Chemical group 0.000 claims description 26
• 229910052740 iodine Inorganic materials 0.000 claims description 24
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 22
• 230000001012 protector Effects 0.000 claims description 19
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 18
• 239000008194 pharmaceutical composition Substances 0.000 claims description 16
• 238000003756 stirring Methods 0.000 claims description 16
• 206010028980 Neoplasm Diseases 0.000 claims description 15
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 14
• 150000002148 esters Chemical class 0.000 claims description 11
• 150000001412 amines Chemical class 0.000 claims description 9
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 8
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 8
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 7
• 229910052794 bromium Chemical group 0.000 claims description 7
• 230000006870 function Effects 0.000 claims description 7
• BYYLPECJKOEHBV-UHFFFAOYSA-N 4-(3-chloroanilino)-7h-pyrrolo[2,3-d]pyrimidine-6-carbaldehyde Chemical compound ClC1=CC=CC(NC=2C=3C=C(C=O)NC=3N=CN=2)=C1 BYYLPECJKOEHBV-UHFFFAOYSA-N 0.000 claims description 6
• 241001465754 Metazoa Species 0.000 claims description 6
• 125000004466 alkoxycarbonylamino group Chemical group 0.000 claims description 6
• 150000001448 anilines Chemical class 0.000 claims description 6
• 125000004429 atom Chemical group 0.000 claims description 6
• 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 6
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
• 229910052783 alkali metal Inorganic materials 0.000 claims description 5
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 5
• 229910052799 carbon Inorganic materials 0.000 claims description 5
• 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 5
• 125000004343 1-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
• BNMRACHWXQYRHO-UHFFFAOYSA-N 4-(3-chloroanilino)-7h-pyrrolo[2,3-d]pyrimidine-6-carbothioamide Chemical compound N1=CN=C2NC(C(=S)N)=CC2=C1NC1=CC=CC(Cl)=C1 BNMRACHWXQYRHO-UHFFFAOYSA-N 0.000 claims description 4
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
• 150000001340 alkali metals Chemical class 0.000 claims description 4
• 239000003937 drug carrier Substances 0.000 claims description 4
• OGEBYZFAAZVIHT-UHFFFAOYSA-N N-(3-chlorophenyl)-6-(2H-tetrazol-5-yl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine Chemical compound ClC1=CC=CC(NC=2C=3C=C(NC=3N=CN=2)C=2NN=NN=2)=C1 OGEBYZFAAZVIHT-UHFFFAOYSA-N 0.000 claims description 3
• 125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 claims description 3
• 125000005036 alkoxyphenyl group Chemical group 0.000 claims description 3
• 150000001351 alkyl iodides Chemical class 0.000 claims description 3
• 239000012024 dehydrating agents‎ Substances 0.000 claims description 3
• PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims description 3
• 150000002443 hydroxylamines Chemical class 0.000 claims description 3
• 239000012948 isocyanate Substances 0.000 claims description 3
• CFHGBZLNZZVTAY-UHFFFAOYSA-N lawesson's reagent Chemical compound C1=CC(OC)=CC=C1P1(=S)SP(=S)(C=2C=CC(OC)=CC=2)S1 CFHGBZLNZZVTAY-UHFFFAOYSA-N 0.000 claims description 3
• VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims description 3
• YYELWCZQXDCXCI-UHFFFAOYSA-N 1-[3-[4-(3-chloroanilino)-7h-pyrrolo[2,3-d]pyrimidin-6-yl]phenyl]-3-ethylurea Chemical compound CCNC(=O)NC1=CC=CC(C=2NC3=NC=NC(NC=4C=C(Cl)C=CC=4)=C3C=2)=C1 YYELWCZQXDCXCI-UHFFFAOYSA-N 0.000 claims description 2
• UTIXVEICQYJJRY-UHFFFAOYSA-N 1-[3-[4-(3-chloroanilino)-7h-pyrrolo[2,3-d]pyrimidin-6-yl]phenyl]-3-methylthiourea Chemical compound CNC(=S)NC1=CC=CC(C=2NC3=NC=NC(NC=4C=C(Cl)C=CC=4)=C3C=2)=C1 UTIXVEICQYJJRY-UHFFFAOYSA-N 0.000 claims description 2
• TWNRMTYWTBYQQS-UHFFFAOYSA-N 1-[4-[4-(3-chloroanilino)-7h-pyrrolo[2,3-d]pyrimidin-6-yl]phenyl]-3-ethylurea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(NC1=NC=N2)=CC1=C2NC1=CC=CC(Cl)=C1 TWNRMTYWTBYQQS-UHFFFAOYSA-N 0.000 claims description 2
• UCRKSQGCZVGBGX-UHFFFAOYSA-N 1-[4-[4-(3-chloroanilino)-7h-pyrrolo[2,3-d]pyrimidin-6-yl]phenyl]-3-methylthiourea Chemical compound C1=CC(NC(=S)NC)=CC=C1C(NC1=NC=N2)=CC1=C2NC1=CC=CC(Cl)=C1 UCRKSQGCZVGBGX-UHFFFAOYSA-N 0.000 claims description 2
• CGSVJQVCEGIWCF-OAHLLOKOSA-N 1-ethyl-3-[3-[4-[[(1r)-1-phenylethyl]amino]-7h-pyrrolo[2,3-d]pyrimidin-6-yl]phenyl]urea Chemical compound CCNC(=O)NC1=CC=CC(C=2NC3=NC=NC(N[C@H](C)C=4C=CC=CC=4)=C3C=2)=C1 CGSVJQVCEGIWCF-OAHLLOKOSA-N 0.000 claims description 2
• YPCURGZEPMFYLX-OAHLLOKOSA-N 1-ethyl-3-[4-[4-[[(1r)-1-phenylethyl]amino]-7h-pyrrolo[2,3-d]pyrimidin-6-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(NC1=NC=N2)=CC1=C2N[C@H](C)C1=CC=CC=C1 YPCURGZEPMFYLX-OAHLLOKOSA-N 0.000 claims description 2
• VEJBANJNCNEZHG-CQSZACIVSA-N 1-methyl-3-[3-[4-[[(1r)-1-phenylethyl]amino]-7h-pyrrolo[2,3-d]pyrimidin-6-yl]phenyl]thiourea Chemical compound CNC(=S)NC1=CC=CC(C=2NC3=NC=NC(N[C@H](C)C=4C=CC=CC=4)=C3C=2)=C1 VEJBANJNCNEZHG-CQSZACIVSA-N 0.000 claims description 2
• CYMAZKIEYPVYOH-UHFFFAOYSA-N 2-methoxy-4-[4-(3-methylanilino)-7h-pyrrolo[2,3-d]pyrimidin-6-yl]phenol Chemical compound C1=C(O)C(OC)=CC(C=2NC3=NC=NC(NC=4C=C(C)C=CC=4)=C3C=2)=C1 CYMAZKIEYPVYOH-UHFFFAOYSA-N 0.000 claims description 2
• VAKYVBRASQJLDI-UHFFFAOYSA-N 2-methylpropyl n-[4-[4-(3-chloroanilino)-7h-pyrrolo[2,3-d]pyrimidin-6-yl]phenyl]carbamate Chemical compound C1=CC(NC(=O)OCC(C)C)=CC=C1C(NC1=NC=N2)=CC1=C2NC1=CC=CC(Cl)=C1 VAKYVBRASQJLDI-UHFFFAOYSA-N 0.000 claims description 2
• JEWOIKNJTXJTGH-UHFFFAOYSA-N 4-(4-anilino-7h-pyrrolo[2,3-d]pyrimidin-6-yl)-2-methoxyphenol;hydrochloride Chemical compound Cl.C1=C(O)C(OC)=CC(C=2NC3=NC=NC(NC=4C=CC=CC=4)=C3C=2)=C1 JEWOIKNJTXJTGH-UHFFFAOYSA-N 0.000 claims description 2
• WXZNMFZVZMNGIO-UHFFFAOYSA-N 4-[4-(3-chloroanilino)-7h-pyrrolo[2,3-d]pyrimidin-6-yl]-2-methoxyphenol;hydrochloride Chemical compound Cl.C1=C(O)C(OC)=CC(C=2NC3=NC=NC(NC=4C=C(Cl)C=CC=4)=C3C=2)=C1 WXZNMFZVZMNGIO-UHFFFAOYSA-N 0.000 claims description 2
• 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 2
• VGFSMURRDQKEKB-UHFFFAOYSA-N 6-(3-methoxy-4-phenylmethoxyphenyl)-n-(3-methylphenyl)-7h-pyrrolo[2,3-d]pyrimidin-4-amine Chemical compound COC1=CC(C=2NC3=NC=NC(NC=4C=C(C)C=CC=4)=C3C=2)=CC=C1OCC1=CC=CC=C1 VGFSMURRDQKEKB-UHFFFAOYSA-N 0.000 claims description 2
• QOLIVYYSALQXGF-LJQANCHMSA-N 6-[3-(benzylamino)phenyl]-n-[(1r)-1-phenylethyl]-7h-pyrrolo[2,3-d]pyrimidin-4-amine Chemical compound N([C@H](C)C=1C=CC=CC=1)C(C=1C=2)=NC=NC=1NC=2C(C=1)=CC=CC=1NCC1=CC=CC=C1 QOLIVYYSALQXGF-LJQANCHMSA-N 0.000 claims description 2
• NIFHYNGZYDVDBU-UHFFFAOYSA-N 6-[4-(benzylamino)phenyl]-n-(3-chlorophenyl)-7h-pyrrolo[2,3-d]pyrimidin-4-amine Chemical compound ClC1=CC=CC(NC=2C=3C=C(NC=3N=CN=2)C=2C=CC(NCC=3C=CC=CC=3)=CC=2)=C1 NIFHYNGZYDVDBU-UHFFFAOYSA-N 0.000 claims description 2
• PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 2
• QOPHSBUZTVLVBJ-UHFFFAOYSA-N N-(3-chlorophenyl)-6-(1-methyltetrazol-5-yl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine Chemical compound CN1N=NN=C1C(NC1=NC=N2)=CC1=C2NC1=CC=CC(Cl)=C1 QOPHSBUZTVLVBJ-UHFFFAOYSA-N 0.000 claims description 2
• BCZCVGXQOLPACI-UHFFFAOYSA-N N-(3-chlorophenyl)-6-(2-methyltetrazol-5-yl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine Chemical compound CN1N=NC(C=2NC3=NC=NC(NC=4C=C(Cl)C=CC=4)=C3C=2)=N1 BCZCVGXQOLPACI-UHFFFAOYSA-N 0.000 claims description 2
• GAABGZUDSKAVGH-UHFFFAOYSA-N N-(3-chlorophenyl)-6-(4,5-dimethyl-1,3-thiazol-2-yl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine Chemical compound S1C(C)=C(C)N=C1C(NC1=NC=N2)=CC1=C2NC1=CC=CC(Cl)=C1 GAABGZUDSKAVGH-UHFFFAOYSA-N 0.000 claims description 2
• ZRSLTYRSYOZHIR-UHFFFAOYSA-N N-(3-chlorophenyl)-6-(4-ethyl-1,3-thiazol-2-yl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine Chemical compound CCC1=CSC(C=2NC3=NC=NC(NC=4C=C(Cl)C=CC=4)=C3C=2)=N1 ZRSLTYRSYOZHIR-UHFFFAOYSA-N 0.000 claims description 2
• BPEIBTXCKPKWLE-UHFFFAOYSA-N N-(3-chlorophenyl)-6-[4-(4-methoxyphenyl)-1,3-thiazol-2-yl]-7H-pyrrolo[2,3-d]pyrimidin-4-amine Chemical compound C1=CC(OC)=CC=C1C1=CSC(C=2NC3=NC=NC(NC=4C=C(Cl)C=CC=4)=C3C=2)=N1 BPEIBTXCKPKWLE-UHFFFAOYSA-N 0.000 claims description 2
• DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims description 2
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
• NUXWAOSDMYECDX-UHFFFAOYSA-N ethyl n-[4-[4-(3-chloroanilino)-7h-pyrrolo[2,3-d]pyrimidin-6-yl]phenyl]carbamate Chemical compound C1=CC(NC(=O)OCC)=CC=C1C(NC1=NC=N2)=CC1=C2NC1=CC=CC(Cl)=C1 NUXWAOSDMYECDX-UHFFFAOYSA-N 0.000 claims description 2
• 150000002513 isocyanates Chemical class 0.000 claims description 2
• 150000002540 isothiocyanates Chemical class 0.000 claims description 2
• ROZJWSLFOMITNR-UHFFFAOYSA-N methyl n-[4-[4-(3-chloroanilino)-7h-pyrrolo[2,3-d]pyrimidin-6-yl]phenyl]carbamate Chemical compound C1=CC(NC(=O)OC)=CC=C1C(NC1=NC=N2)=CC1=C2NC1=CC=CC(Cl)=C1 ROZJWSLFOMITNR-UHFFFAOYSA-N 0.000 claims description 2
• SDSLGPIDULPJQG-MRXNPFEDSA-N n,n-dimethyl-n'-[3-[4-[[(1r)-1-phenylethyl]amino]-7h-pyrrolo[2,3-d]pyrimidin-6-yl]phenyl]methanimidamide Chemical compound N([C@H](C)C=1C=CC=CC=1)C(C=1C=2)=NC=NC=1NC=2C1=CC=CC(N=CN(C)C)=C1 SDSLGPIDULPJQG-MRXNPFEDSA-N 0.000 claims description 2
• PRVIBBCNUUBOSX-UHFFFAOYSA-N n-(3-chlorophenyl)-6-(1,3-thiazol-2-yl)-7h-pyrrolo[2,3-d]pyrimidin-4-amine Chemical compound ClC1=CC=CC(NC=2C=3C=C(NC=3N=CN=2)C=2SC=CN=2)=C1 PRVIBBCNUUBOSX-UHFFFAOYSA-N 0.000 claims description 2
• LIPUGMMVKJZMRG-UHFFFAOYSA-N n-(3-chlorophenyl)-6-(3-methoxy-4-phenylmethoxyphenyl)-7h-pyrrolo[2,3-d]pyrimidin-4-amine Chemical compound COC1=CC(C=2NC3=NC=NC(NC=4C=C(Cl)C=CC=4)=C3C=2)=CC=C1OCC1=CC=CC=C1 LIPUGMMVKJZMRG-UHFFFAOYSA-N 0.000 claims description 2
• GBCGNNNFIRWGCW-UHFFFAOYSA-N n-(3-chlorophenyl)-6-[4-[(4-methylpiperazin-1-yl)methylideneamino]phenyl]-7h-pyrrolo[2,3-d]pyrimidin-4-amine Chemical compound C1CN(C)CCN1C=NC1=CC=C(C=2NC3=NC=NC(NC=4C=C(Cl)C=CC=4)=C3C=2)C=C1 GBCGNNNFIRWGCW-UHFFFAOYSA-N 0.000 claims description 2
• ROLDUDKLNYYONL-UHFFFAOYSA-N n-[3-[4-(3-chloroanilino)-7h-pyrrolo[2,3-d]pyrimidin-6-yl]phenyl]ethanesulfonamide Chemical compound CCS(=O)(=O)NC1=CC=CC(C=2NC3=NC=NC(NC=4C=C(Cl)C=CC=4)=C3C=2)=C1 ROLDUDKLNYYONL-UHFFFAOYSA-N 0.000 claims description 2
• RBEFWIDYHAIBSL-UHFFFAOYSA-N n-[3-[4-(3-chloroanilino)-7h-pyrrolo[2,3-d]pyrimidin-6-yl]phenyl]methanesulfonamide Chemical compound CS(=O)(=O)NC1=CC=CC(C=2NC3=NC=NC(NC=4C=C(Cl)C=CC=4)=C3C=2)=C1 RBEFWIDYHAIBSL-UHFFFAOYSA-N 0.000 claims description 2
• PKNAMUVGIGLHAY-UHFFFAOYSA-N n-[3-[4-(3-chloroanilino)-7h-pyrrolo[2,3-d]pyrimidin-6-yl]phenyl]propane-2-sulfonamide Chemical compound CC(C)S(=O)(=O)NC1=CC=CC(C=2NC3=NC=NC(NC=4C=C(Cl)C=CC=4)=C3C=2)=C1 PKNAMUVGIGLHAY-UHFFFAOYSA-N 0.000 claims description 2
• WVICNPJYDFMIGL-OAHLLOKOSA-N n-[3-[4-[[(1r)-1-phenylethyl]amino]-7h-pyrrolo[2,3-d]pyrimidin-6-yl]phenyl]ethanesulfonamide Chemical compound CCS(=O)(=O)NC1=CC=CC(C=2NC3=NC=NC(N[C@H](C)C=4C=CC=CC=4)=C3C=2)=C1 WVICNPJYDFMIGL-OAHLLOKOSA-N 0.000 claims description 2
• KQWSURRAHQPGAF-CQSZACIVSA-N n-[3-[4-[[(1r)-1-phenylethyl]amino]-7h-pyrrolo[2,3-d]pyrimidin-6-yl]phenyl]methanesulfonamide Chemical compound N([C@H](C)C=1C=CC=CC=1)C(C=1C=2)=NC=NC=1NC=2C1=CC=CC(NS(C)(=O)=O)=C1 KQWSURRAHQPGAF-CQSZACIVSA-N 0.000 claims description 2
• WLMINMLKCZPIDN-UHFFFAOYSA-N n-[4-[4-(3-chloroanilino)-7h-pyrrolo[2,3-d]pyrimidin-6-yl]phenyl]benzenesulfonamide Chemical compound ClC1=CC=CC(NC=2C=3C=C(NC=3N=CN=2)C=2C=CC(NS(=O)(=O)C=3C=CC=CC=3)=CC=2)=C1 WLMINMLKCZPIDN-UHFFFAOYSA-N 0.000 claims description 2
• NDIAGRBKTSAOQM-UHFFFAOYSA-N n-[4-[4-(3-chloroanilino)-7h-pyrrolo[2,3-d]pyrimidin-6-yl]phenyl]propane-2-sulfonamide Chemical compound C1=CC(NS(=O)(=O)C(C)C)=CC=C1C(NC1=NC=N2)=CC1=C2NC1=CC=CC(Cl)=C1 NDIAGRBKTSAOQM-UHFFFAOYSA-N 0.000 claims description 2
• ZXEAZQRLYXDOIU-OAHLLOKOSA-N n-[4-[4-[[(1r)-1-phenylethyl]amino]-7h-pyrrolo[2,3-d]pyrimidin-6-yl]phenyl]ethanesulfonamide Chemical compound C1=CC(NS(=O)(=O)CC)=CC=C1C(NC1=NC=N2)=CC1=C2N[C@H](C)C1=CC=CC=C1 ZXEAZQRLYXDOIU-OAHLLOKOSA-N 0.000 claims description 2
• KJPHJVDDQOMOSH-MRXNPFEDSA-N n-[4-[4-[[(1r)-1-phenylethyl]amino]-7h-pyrrolo[2,3-d]pyrimidin-6-yl]phenyl]propane-2-sulfonamide Chemical compound C1=CC(NS(=O)(=O)C(C)C)=CC=C1C(NC1=NC=N2)=CC1=C2N[C@H](C)C1=CC=CC=C1 KJPHJVDDQOMOSH-MRXNPFEDSA-N 0.000 claims description 2
• MKLSHESXKCZSML-UHFFFAOYSA-N propan-2-yl n-[4-[4-(3-chloroanilino)-7h-pyrrolo[2,3-d]pyrimidin-6-yl]phenyl]carbamate Chemical compound C1=CC(NC(=O)OC(C)C)=CC=C1C(NC1=NC=N2)=CC1=C2NC1=CC=CC(Cl)=C1 MKLSHESXKCZSML-UHFFFAOYSA-N 0.000 claims description 2
• JJJQHTCJNMSSJV-UHFFFAOYSA-N pyrrolo[2,3-d]pyrimidin-4-one Chemical class O=C1N=CN=C2N=CC=C12 JJJQHTCJNMSSJV-UHFFFAOYSA-N 0.000 claims description 2
• 150000004943 pyrrolo[2,3-d]pyrimidines Chemical class 0.000 claims description 2
• 230000001225 therapeutic effect Effects 0.000 claims description 2
• LDUVGYTUBRSPKL-UBKPWBPPSA-N (NE)-N-[[4-(3-chloroanilino)-7H-pyrrolo[2,3-d]pyrimidin-6-yl]methylidene]hydroxylamine Chemical compound N1=CN=C2NC(/C=N/O)=CC2=C1NC1=CC=CC(Cl)=C1 LDUVGYTUBRSPKL-UBKPWBPPSA-N 0.000 claims 1
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